Abstract
Tetraalkyl-substituted (E, E)-buta-1,3-dienes were synthesized regio- and stereoselectively by the tantalum(V) chloride-catalyzed reaction of dialkyl-substituted acetylenes with EtAlCl2 and sodium metal in toluene followed by hydrolysis or deuterolysis. A mechanism of these transformations was suggested. The in situ generated organoaluminum intermediates reacted with methylsulfonyl chloride and iodine to give tetraalkyl-substituted (Z,Z)-1,4-dichlorobuta-1,3-dienes and 1,4-diiodobuta-1,3-dienes, respectively.
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Funding
This work was financially supported by the Russian Science Foundation (Project No. 19-73-10113). Recrystallization of tantalum(V) chloride37 and drying of toluene were performed in the framework of the state assignment from the Ministry of Science and Higher Education of the Russian Federation (FMRS-2022-0076).
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2149–2155, October, 2022.
No human or animal subjects were used in this research.
The authors declare no competing interests.
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Kadikova, R.N., Ramazanov, I.R., Amirova, A.K. et al. Tantalum-catalyzed reaction of disubstituted acetylenes with EtAlCl2. Russ Chem Bull 71, 2149–2155 (2022). https://doi.org/10.1007/s11172-022-3640-x
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DOI: https://doi.org/10.1007/s11172-022-3640-x